Advertisement

What It's Like to Be One of the First 10 Employees at a Successful Startup

If you're offered a seat on a rocket ship, you don't ask what seat. You just get on.

This advice from Google Executive Chairman Eric Schmidt is one of the standout lines from Sheryl Sandberg’s Lean In. The Fortune 500 COO says it's some of the best career advice she's ever received — after all, it landed her at Google and then Facebook.

But there are rocket ships beyond Silicon Valley, and for our new series The First 100, we tracked down the first 100 employees at 100 startups and small businesses. These are the early employees who wore many hats, laid the foundation and established the culture for some of the coolest businesses around. We asked each of them questions about their ride on the rocket ship, and over the next few weeks, you'll get to know 100 faces behind your favorite companies. Below, meet employees 1 through 10 at innovative businesses including Of a Kind, Reddit, Groupon and Plated. Stay tuned for the rest of the First 100 here.

Watch the video above to hear about Michelle's experiences at HowAboutWe

A more relatable company... I spent five years at a few different parenting magazines, and I really enjoyed my time working with great editors and writers at those magazines, but I was excited to join a company that was more aligned with my personal interests — dating vs. parenting. And it was also exciting to join a startup. At my first job, I remember thinking I'd never join a company that wasn't affiliated with a magazine — I only wanted to work on magazine websites. But I moved to New York City and started getting into social media and the startup scene, and I found this opportunity to get involved in something right as it was starting up, which was great.

Facilitating love... HowAboutWe started as a dating site for people to go online to get offline. So many other dating sites are meant to just keep you online communicating there forever, and that's not a great way to get to know someone. But, posting a fun date idea, like "How about we go search for the best mulled wine on the Lower East Side," that gives you insight into what that person is like and wants to do, and it gives you a natural entry point to get offline. And so that has always been the core mission of the dating site. I love hearing the success stories of happy couples and it really makes me tear up-like I had something to do with that. It’s kind of a crazy thing.

The road to Branch... I've always bounced between media and technology. Before I joined Branch, I was at Hearst Ventures, the venture capital wing of Hearst Corporation. Before that, I worked for The New York Times and two technology startups as an intern. Josh and the other founders had a lot to say about both, but even though they had a really good idea of the problem they wanted to solve, they weren't committed to one solution. I liked that approach a lot. It allowed for us all to be curious and ask questions and explore, and by joining early, I got to be a part of that process, too. Plus they were really solid people, and that always wins out.

In the beginning... my role was really flexible by design — pretty much anything from design research to business development fell onto my plate. That flexibility was super valuable to me and to the company, but I also learned pretty quickly that it meant I had to be even more proactive about what I was spending my time on. A startup's priorities are always changing, and figuring out how to be helpful this month (or even this week) was sometimes easier said than done. That was most apparent when we decided to build an entirely new product called Potluck, which required much more community management than it did business development.

The first non-technical hire... Working with engineers is so much fun. I'm constantly surprised by how much division there is at companies between technical and non-technical people, and I think that's a real shame. Being on such a small team with people whose skill sets are so unlike yours forces you to constantly be translating what you're doing to help them understand you, and make sure you understand them. Forming that shared vocabulary was such an interesting process, and was something Jason Goldman put a lot of emphasis on. I also got asked about grammar a lot.

On being #3... I had previously worked in the customer experience department at Bonobos (I was a ninja!) and before that, the community team at Foursquare. Both were great experiences, but the companies were already large enough that they had already established the groundwork for everything. I, on the other hand, wanted to be a part of actually laying down the groundwork — which is what I get to do at Of a Kind! There’s so much opportunity for me to tweak or adjust how we do things, and everything we do feels experimental in some way or form. I was also super excited about working for a company whose mission I admired. There’s an enormous amount of talent out there that isn't getting the attention it deserves, and we get to help expose it — I love being a part of that.

A growing role... In addition to customer relations, I now also handle Of a Kind Collections, which was only in beta when I started. Since the launch, I’ve facilitated relationships between us and all our current Collections designers. I walk them through the on-boarding process, and remain as their point-of-contact for anything Collections-related (technical difficulties, order changes, shipping and fulfillment, etc.). It made sense for me to be the one who manages these relationships, because in a way, these designers are customers too. We want to make sure they’re having a good experience with us no matter what. I also frequently need to contact designers about specific questions from customers (whether it’s about sizing, fit, care instructions), and it's much more efficient for me to take care of everything in one fell swoop.

On "growing up"... We’re having to implement more things that are "formalities" for companies. We just got an employee handbook, and we started having 1-on-1 meetings with [founders] Claire Mazur and Erica Cerulo, which have been helpful. Don't get me wrong, I've never felt like this wasn't a real job. But it's small things like this that make me feel like we're really growing up!

Company culture... The culture is super laid-back, which is just how I like it! It’s the perfect amount of office-ness. It’s not a playground by any means, but I also don’t feel like I’m coming to work in the typical 9-5 corporate environment with cubicles everywhere. We have an open floor plan so we can see each other and talk to each other all the time. We’re a little family! Conversations tend to be about work for the most part, but we also discuss things such as Scandal, Justin Bieber and Beyonce — all very important topics for us. And we consume lots of popcorn. We're big on snacks.

A lean team... The size was almost a relief after working against traditional systems set in place that did not evolve or adapt to changing consumers. It was refreshing (if scary!) to be able to start from the beginning and develop an agile process. FSC offered me the opportunity to focus 100% of my energy toward online marketing. This allowed me more time to hone best practices, research new developments and learn search marketing from an expert in the field.

Growing pains... We've grown from 4 to 18 and the hardest part was probably the shift from 4 to 8. There is a point where you have to delegate and lose control, but it was an opportunity to create a really strong process and put protocols in place for accountability and consistency. We are continually identifying new areas of opportunity to expand and grow. We've created unique positions that not only meet these agency needs, but, also provide growth opportunities that play to our employees’ strengths and keep them challenged and happy. We recently created a new division called Empowerment to meet small business needs. As we bring on larger retainer accounts, we are still dedicated to the original mission to help accomplish business goals through online marketing.

Cutting loose... Every Thursday at 4:00 the agency meets for Power Hour to discuss industry trends, share lessons learned and we don’t leave without creating a unique piece of content that expresses our agency personality, from a Drake hands video to a 12 Days of FSC Christmas song. We encourage positive feedback and have a dedicated Wall of Win for staff to post sticky notes calling out other team member’s contributions and successes. It’s a pretty stellar place to work.

The path to Reddit... Before Reddit I was working for Palm Pictures, an indie film and music company, as well as consulting for various indie, documentary and foreign film distributors. Like everyone who is working at Reddit now, I was a hopeless addict and fan before I started working here. Soon after Reddit launched, I cold emailed the site offering to help if there was anything I could do. That led to meeting up with Alexis Ohanian (co-founder), and then eventually I worked for Reddit on some smaller projects. In October 2008, they offered me a part-time job as Community Manager. Even though the pay was basically nothing, I loved the site and the community and the team, so it was a very easy decision to join.

Why I'm still here... Each day is different and somewhat unpredictable and the users keep taking the simple but flexible platform in new directions. Also, we are extremely lucky to have an outstanding team who are all here because we love Reddit. What more could someone ask for?

On the past six years... A lot has changed around us, but the company hasn't really changed that much. We've grown from 5 employees when I joined to around 40 now, and we've gone through various corporate stages from being part of Conde Nast to now being an independent company, but the basics are pretty much the same. We're still figuring things out as we go and trying to have fun while we're doing it.

A fortuitous meeting... After six years, I left Etsy on a Thursday, and I met the BarkBox founders, Matt Meeker, Henrik Werdelin and Carly Strife, on Friday. I sat down with them at a table, thinking I could get some free stuff for the dog rescue I helped run; instead, I had a real conversation with three real, innovative, brilliant and hilarious people. They made me feel like I was one of them. Out of habit, I started spouting off ideas to grow BarkBox and help dogs in need and they listened. They threw ideas back at me and I was inspired to work with them. BarkBox hired me to focus on helping dogs in need — spending the 10% we give to shelters and rescues thoughtfully. While I was creating the BarkBox "Customer Love" team, I started a fundraising program for shelters and rescues. We soon found those who were referred to BarkBox through shelters and rescues, were our best "pupscribers" and I am now able to really focus on what I was originally brought here to do. I just put a six-month plan together — it's so bloody exciting. BarkBox just sent 165 checks to small county shelters and volunteer-run dog rescues. Stuffing an envelope never felt so rewarding. Every month I get to send out more.

The keys to growing well... You have to be able to trust your team, and the vision for the company. That's what you need to hold on to, through the first wild year. You have to be comfortable with both making high level decisions on a daily basis, and cleaning up an office dog's pee. Growing a company? Hire the right people. Hire people that have enough balls to tell you an idea is terrible, and make sure they are the kind of person that can take this kind of feedback, too. There's a certain amount of crazy you need to have — and a dedication to that crazy. When I said I wanted to bringing fifty puppies to NYC from a kill shelter in Alabama and sell (adoption fees were donated to shelters and rescues involved) them in a pop-up shop in Soho, the BarkBox founders said, go for it. (And they seemed genuinely shocked when I made that happen 60 days later.)

Dogs in the office... You'll get less work done at first. Some dogs will sleep all day in their beds under your desk, most will be anxious, annoying — they'll pee in front of everyone in the middle of a meeting. It will take patience and guidance to get your dog to be a good office dog. Then you'll get more work done because you won't have to go home at 6:30 to take the dog out. Plus, work is just better when your dog is snoozin' on your lap. They're also great for check-out-how-cool-our-office-is photo shoots.

Keeping it cool... I have moments of preemptive anxiety, thinking about growing into a different company — losing some of the magic that is here now. I am confident though, if any team could keep this pace, energy and innovation alive as we grow, it's BarkBox. There are a few of us here are BarkBox that have been early startup employees in the past, and we are on high alert, nipping signs of structured organization in the bud. "Should we have a schedule for dogs in the office? There's so many of us now." Nah, let's just wing it. If your dog is annoying, we'll just tell you to not bring them back.

An amazing evolution... My first week on the job, I was sitting Indian-style on the floor measuring product dimensions with a pair of calipers so we could get shipping cartons quoted for our first big retail shipment. Interns were building their own desks in the kitchen and we were still trying to prove to the world that we could make invention accessible by shipping a flexible power strip. Four years later, we're developing cutting-edge connected home products with one of the greatest brands in American history, GE. We're partnered with the best retailers in the world and have managed to grow from a $1M company to a $48M company during my time here. We’ve transitioned from being the early-stage startup doing whatever it takes to book the first million of revenue to being the maturing startup doing whatever it takes to position the company to scale and truly change the world.

Wearing many hats... The position I applied for was for an “Inventory Ninja.” In a startup with fewer than 10 people, a title is just a title and it rarely represents everything you do in your day-to-day work. Throughout my time at Quirky, I’ve managed inventory accounting, logistics, production, demand planning, brand management, project management, you name it. As of two weeks ago, I became the General Manager of GE + Quirky, where I will be managing a team at Quirky to develop co-branded connected devices in partnership with GE.

Passion drives everything... There’s not a week that goes by where I’m not completely blown away by something we’ve accomplished (given our resources and pace). The sheer amount of talent, creativity and passion at this company is humbling, and something tells me it's unlike anything I'll experience at most other companies. I’ve found an environment where I get to break, make, learn, build, inspire and help change the world. I’d be crazy to ever walk away — this is what every little kid dreams of doing when they grow up.

Doing the "impossible"... Don't ever let anyone (internally or externally) convince you that what you’re trying to do is impossible, because it’s not true. As an early member of the company, you'll go through some damn hard things and you'll inevitably question yourself when it seems like everything is falling apart. Later on, you’ll realize that those very experiences allow you to appreciate where you are today and remain humble. Don’t ever lose sight of that feeling; make sure that you’re doing everything you can to maintain that perseverance as you expand your team.

The path to Plated... I've always been a foodie…but I was working for a real estate developer and landlord. At the time there wasn't much financing available, so new projects were scarce. In between loan modifications and refinancings, I stumbled across Plated.com… It had always blown my mind that I couldn’t walk into a super market and purchase a grouping of ingredients that could easily be made into a meal at home. Plated was aiming to change this. I had to find a way to join for my sanity's sake.

Started from the bottom... When I first started at Plated, I was mixing, measuring and packing. After a few weeks I was researching food regulations, searching for new facilities, helping onboard new employees, managing insurance policies, editing recipes, searching for new vendors, onboarding new couriers, codifying and enhancing our quality assurance program…and loving every minute of it. Taking on new responsibilities is easy, because there is no other choice when the team is small. As we've grown, the tough part has been giving up responsibilities … but luckily, the Plated Team is jam-packed with all-stars.

Eating the dog food... I do order Plated every week. There are some weeks when travel or other commitments prevent me from cooking every meal. Even when I won’t be able to cook everything, I always want to get a sense of the un-boxing experience and how the ingredients arrive to the consumer. The only way to produce a quality product is to put it under a microscope every single day. If you read the feedback we get on social media, it’s easy to see that we're changing people's lives. Knowing that your job results in bringing people back into the kitchen and getting them cooking delicious meals together is plenty to get me out of bed in the morning.

The hunt for a warehouse... Finding and building out our new fulfillment center in the South Bronx has been my most exciting project at Plated. It took three months looking in all five Boroughs, New Jersey and Pennsylvania to find something that suited our needs and price point. I had worked on many lease negotiations, and construction projects before. But, this was the first time doing it without a seasoned real estate veteran making the final decisions. Nick and Josh deferred to my judgment (while at the same time asking heaps of questions), and we ended up with an amazing facility. Turning the once beat-up warehouse into a first-class food-grade facility has been one of the most fulfilling experiences of my career.

A new idea... I had a unique vantage point of the birth of Groupon because the company was founded out of Lightbank, where I worked for Groupon CEO and co-founder Eric Lefkofsky. Ultimately, we focused on local commerce and shifted our attention from collective action to collective buying. When you’re doing something that no one has ever done before, it could be unsettling — no playbook existed, were we doing it right? But at the same time, everyone believed in what we were doing.

Jumping on the rocket ship...In the early days of a startup it’s controlled chaos and employees need to be willing to pitch in as needed to develop new teams and departments that will help the company grow. As one of the only non-developers in the early days of Groupon, I ran human resources, facilities, construction, buildouts, accounting, payroll, among other things in addition to providing executive support. It’s been a rewarding experience for me to hand off some of the early hats that I wore at the company and to see entire departments with hundreds of people spring up to support the company.

Going public... The IPO was an exhilarating experience and provoked an enormous sense of pride. Being at the NASDAQ exchange when we rang the opening bell with all of the early employees and our very first Groupon merchant (Motel Bar in Chicago) is a moment I'll never forget. Seriously — how many people have the opportunity to do something like that?

Job seeking... I had recently moved from London to New York, and I contacted Apploi's CEO, Adam Lewis because I admired the founding objectives of the company — to allow job seekers to shine, grow and find jobs; and for organizations to effectively reach the people they need. I was excited for the challenge of working for a company that is continually evolving and that ultimately could have a huge impact on unemployment in America and indeed the world.

An evolving role... When I began at Apploi I was managing the content for the Apploi-Observer, providing unique content in the form of career advice, news feature articles and videos for the Apploi community. As the members became more actively engaged, it was clear that there was a great opportunity to cultivate a relationship with the members, engaging with them to support each one on their new jobs and their career paths. The role then evolved into managing the overall engagement with the Apploi community.

Creating better solutions... Apploi has evolved hugely since I began, but the original objectives, values and aspirations of Apploi have remained the same. While it was clear when Apploi was started that there were vast problems in the way companies hired and millions of people were left unemployed, the need to solve this issue has only become more apparent. The entire team feels this responsibility and strives to confront it together. The change is most noticeable in our partnerships, clients and members, which are growing at an extremely fast rate. Furthermore, our members are becoming increasingly engaged.

Today, Apploi has 24 employees.

Were you one of the early employees at your company? Tell us about your experience in the comments, and check back next week to meet employees #11-20.

Mashable
is a global, multi-platform media and entertainment company. Powered by its own proprietary technology, Mashable is the go-to source for tech, digital culture and entertainment content for its dedicated and influential audience around the globe.